Hydrazine hydrate (1:1) → 5-amino-3-((4-(dimethylamino)phenyl)amino)-1H-pyrazole-4-carboxamide

HRID 1049158Notes

Reaction equation

HRID 1049158 reaction equation
[C:1]([C:3](=[C:7]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=1)SC)[C:4]([NH2:6])=[O:5])#[N:2].O.[NH2:21][NH2:22]>C(O)C>[NH2:2][C:1]1[NH:22][N:21]=[C:7]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=2)[C:3]=1[C:4]([NH2:6])=[O:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 867018642-Cyano-3-((4-(dimethylamino)phenyl)amino)-3-(methylthio)acrylamide

Product 1

HCID 867018655-amino-3-((4-(dimethylamino)phenyl)amino)-1H-pyrazole-4-carboxamideYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

2-cyano-3-((4-(dimethylamino)phenyl)amino)-3-(methylthio)acrylamide (0.997 g) was suspended in 10 mL of ethanol and hydrazine hydrate (337 μL, 1.5 eq.) was added drop wise to the reaction. The reaction was then heated at 75° C. until the starting material was no longer present and confirmed via HPLC. Once starting material was absent (18 hrs), reaction was brought to room temperature and filtered to obtain 5-amino-3-((4-(dimethylamino)phenyl)amino)-1H-pyrazole-4-carboxamide as an off white to yellow powder. The product was allowed to dry under vacuum for 1 hr (900 mg, 72% yield).

Workup

  1. customwise to the reaction
  2. custom(18 hrs), reaction
  3. customwas brought to room temperature
  4. filtrationfiltered

Sources & evidence

ORD record
ord-28efc1b79d6e4df29d9be3845dd7db0d
Source dataset
uspto-grants-2016_07
Patent number
US09382237B2

Reaction notes

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